2-[(Thiophen-2-ylmethyl)-amino]-ethanol → 4-[(2-Hydroxy-ethyl)-thiophen-2-ylmethyl-amino]-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester

HRID 1831666Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9](Cl)=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21].[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH2:28][NH:29][CH2:30][CH2:31][OH:32]>CN1CCCC1=O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([N:29]([CH2:30][CH2:31][OH:32])[CH2:28][C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-chloro-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester and 2-[(thiophen-2-ylmethyl)-amino]-ethanol in 1-methyl-2-pyrrolidinone was heated at 130° C. overnight. The mixture was quenched with water, brine and extracted with ethyl acetate. The organic layer was dried and concentrated to dryness. The residue was purified through silica gel column chromatography to give the title compound. 1H NMR (CDCl3) d 7.22(m,1H), 6.94m,2H), 6.84(s,2H), 6.44(s,1H), 4.52(s,2H), 3.91(s,3H), 3.679t,2H), 3.369t,2H), 2.279s,3H), 2.20(s,3H), 2.07(s,6H) ppm.

Workup

customThe mixture was quenched with water, brine
extractionextracted with ethyl acetate
customThe organic layer was dried
concentrationconcentrated to dryness
customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record: ord-46e202f476644b269efde3d8be5af1fe
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067664B1

Reaction notes

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